Sure, I can tell you what little i know. The best, but probably also toughest, place to start is likely the ArchLinux forums.

Wine handles the lifting. Proton, Glorious Eggroll (GE), etc. can be seen as content packs, packing some additional tools and dependencies commonly found in gaming. There exist a lot of other “flavours” of Wine, all with their own specialization, though pure Wine is usually fine for most non-gaming and non-Peripheral (flashing hardware) cases.

The most usefull terms I’ve come across when tinkering are:

• Runner: Location of the specific wine installation. Isn’t actually named “runner”.
• Prefix: Location of the Wine-OS-layer in which the magic will happen. Don’t use the default when tinkering, and clear it when wanting to make a clean attempt.
• wine: Usually found in <runner>/bin/wine. It’s the default way to start executables using wine.
• wineconsole: Found next to wine, opens the executable in a cmd-like console usefull for running .bat files.
• winecfg: Also found next to wine, default configurator for wine, handles dlls, registry, and general settings.
• winetricks: A configuration tool which provides an easy way to install the most well-known dependencies and just functions as a nice “more powerful winecfg”.
• Once Wine is running, C:\\ will be the prefix, and Z:\\ is your Linux computer. You can usually install/run things outside the prefix C:\\, but sometimes it just won’t work, so better try moving it inside if it just don’t wanna.

Running an exe, be it the program you want to get running or a dependency, in the terminal looks something like:

WINEPREFIX="/path/to/my/prefix" "/path/to/runner/bin/wine" "/path/to/executable.exe"

And the neat part is, that to run wine using, say, Proton-GE, you’d just go:

WINEPREFIX="/path/to/my/prefix" "/home/$USER/.local/share/Steam/compatibilitytools.d/GE-Proton8-25/files/bin/wine" "/path/to/executable.exe"

If you want to just use your default WINE installation, you’d leave out the runner part, and just go:

WINEPREFIX="/path/to/my/prefix" "/path/to/executable.exe"

Now, that’s all good and dandy, but who in their right mind uses the terminal anymore?

Bottles, Playonlinux, Lutris, Heroic, and now Steam too (kinda) are launchers which pack some quality of life tools to make creating, running, and tinkering with Wine easier. What launcher you prefer is totally up to you, as they all come with their own ups and downs. Like I stated before, I like Lutris’ Wine runtime packs, but their interface confused me the first time I tried it, so probably not great for starters.

Heroic is nice to look at and simplistic, It doesn’t have a whole bunch of customization options, but it has easy-to-access shortcuts to winetricks and winecfg.

I’ve tried Bottles, and while they provide some appreciated commonly-used dependencies and their user interface is pleasant to look at, they make it unnecessarily difficult to properly tinker with Wine, and for some reason they have to hide and rename everything? Bottles is probably fine for most people, especially for beginners who don’t plan on diving far, but I just couldn’t get comfortable with it.

If you’re tinkering with WINE (or even Proton) using Steam, you’ll probably have a bad time, but they do provide a good collection of games which work out-of-the-box. Not useful for much else wine-related, besides providing Proton and a massive boost to Wine.

At last: Wine logs are weird. I’ll need to learn to read them at some point, but they are so filled with errors and warnings that just naturally exist but don’t attribute to your specific problem that they are borderline useless if you’re not 100% familiar with them. And don’t expect two computers to run an executable the same way just because they use the same Wine runner and Prefix. Wine’s no virtual box.

If anyone knows more, or if I said something factually wrong, then please feel free to correct me.

== Regarding SketchUp ==

I’m not sure how far you got and I’m not sure about your skill level, so please excuse me if you already got this far, but according to WineHQ you’ll need to run a rather lengthy command to get it working. By szilveszter:

Thanks for the comments and help. The program can be installed and used as follows: (1) Installation All selectable languages must be enabled. Even so, an ‘invalid handle’ message is generated, but the installation is completed. (2) Starting the program with NVIDIA graphics processor: __NV_PRIME_RENDER_OFFLOAD=1 __GLX_VENDOR_LIBRARY_NAME=nvidia WINEPREFIX="/DATA/prg/sketchup_2023" WINEESYNC=1 WINEARCH="win64" /opt/wine-staging/bin/wine64 "/DATA/prg/sketchup_2023/drive_c/Program Files/SketchUp/SketchUp 2023/SketchUp.exe" /DisableRubyAPI

So in other words:

1. Download Wine-staging (this can be its own can of worms).
2. Install by first creating the prefix directory, and the running:

$ WINEPREFIX="/home/$USER/<mysketchupwineprefix>" "</path/to/wine-staging-runner/bin/wine>" "</path/to/sketchup_setup.exe>"

Please change the <example> text, and respect the instructions of szilveszter, errors are to be expected.

3. Run the executable using their command, but change /opt/wine-staging/bin/wine64 to where your wine-staging runner is located, and "/DATA/prg/sketchup_2023/drive_c/Program Files/SketchUp/SketchUp 2023/SketchUp.exe" to where you decided to install sketchup. Wine-staging might already be included in regular wine, so with some luck you might be able to use your computers default runner.

As per szilveszter’s instructions, I think it’s wise to install Sketchup inside the prefix.

Also, it appears to be only mostly working, so expect errors and limitations. :(